Traceability is the ability to follow the displacement of food through its entire chain. Extra virgin olive oil (EVOO) represents Italian excellence, with consumers’ increased awareness for traceability. The aim of this work is to propose and analyze the economic sustainability and consumers’ preference of three technological systems supporting traceability: Near Field Communication (NFC) based; tamper-proof device plus Radio Frequency Identification (RFID) and app; QR code tag plus “scratch and win” system and blockchain. An anonymous questionnaire to Italian consumers (n = 1120) was made to acquire consumers’ acceptability of the systems and estimating their willingness to pay additional premium prices for these. An economic analysis estimated and compared the technology costs at different production levels. Results show that 94% of the consumer respondents are interested in the implementation of such technologies, and among them 45% chose QR-code protected by a “scratch-and-win” system with a blockchain infotracing-platform (QR-B). The consumers interested are willing to pay a mean premium price of 17.8% and economic analysis reported evidenced an incidence always lower than mid-/high-production levels. The success of the QR-B could be ascribed to different aspects: the cutting-edge fashion trend of blockchain in the food sector, the use of incentives, the easy-to-use QR-code, and the gamification strategy.